CH485736A - Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate - Google Patents
Verfahren zur Herstellung halogensubstituierter Imidazol-DerivateInfo
- Publication number
- CH485736A CH485736A CH25370A CH2537067A CH485736A CH 485736 A CH485736 A CH 485736A CH 25370 A CH25370 A CH 25370A CH 2537067 A CH2537067 A CH 2537067A CH 485736 A CH485736 A CH 485736A
- Authority
- CH
- Switzerland
- Prior art keywords
- imidazole
- tribromo
- halogen
- trichloro
- formula
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title description 17
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 16
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 description 12
- -1 dialkylcarboxamides Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 230000000895 acaricidal effect Effects 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052717 sulfur Chemical group 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RFTGUQFFTZWXJA-UHFFFAOYSA-N C(CCC)OCN1C(=NC(=C1Cl)Cl)Cl Chemical compound C(CCC)OCN1C(=NC(=C1Cl)Cl)Cl RFTGUQFFTZWXJA-UHFFFAOYSA-N 0.000 description 3
- JQELKFCBGAOGEU-UHFFFAOYSA-N CCCCSCN1C(Cl)=NC(Cl)=C1Cl Chemical compound CCCCSCN1C(Cl)=NC(Cl)=C1Cl JQELKFCBGAOGEU-UHFFFAOYSA-N 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- JERQKRUBRQQLRR-UHFFFAOYSA-N 2,4,5-tribromo-1-(butoxymethyl)imidazole Chemical compound C(CCC)OCN1C(=NC(=C1Br)Br)Br JERQKRUBRQQLRR-UHFFFAOYSA-N 0.000 description 2
- VSMMZLUXWOZHMK-UHFFFAOYSA-N 2,4,5-tribromo-1-(butylsulfanylmethyl)imidazole Chemical compound C(CCC)SCN1C(=NC(=C1Br)Br)Br VSMMZLUXWOZHMK-UHFFFAOYSA-N 0.000 description 2
- DNIQDGBXXYXPGR-UHFFFAOYSA-N 2,4,5-tribromo-1-(methylsulfanylmethyl)imidazole Chemical compound CSCN1C(=NC(=C1Br)Br)Br DNIQDGBXXYXPGR-UHFFFAOYSA-N 0.000 description 2
- TZNNGJTTWOKNKP-UHFFFAOYSA-N 4,5-dibromo-2-chloro-1-(chloromethyl)imidazole Chemical compound ClCN1C(=NC(=C1Br)Br)Cl TZNNGJTTWOKNKP-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
- ZUUKHRCPFPPAQN-UHFFFAOYSA-N CCCCSCN1C(Cl)=NC(Br)=C1Br Chemical compound CCCCSCN1C(Cl)=NC(Br)=C1Br ZUUKHRCPFPPAQN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- HANFGYYVBCDRGL-UHFFFAOYSA-N (2,4,5-tribromoimidazol-1-yl)methanol Chemical compound OCN1C(Br)=NC(Br)=C1Br HANFGYYVBCDRGL-UHFFFAOYSA-N 0.000 description 1
- BQNDPALRJDCXOY-UHFFFAOYSA-N 2,3-dibutylbutanedioic acid Chemical compound CCCCC(C(O)=O)C(C(O)=O)CCCC BQNDPALRJDCXOY-UHFFFAOYSA-N 0.000 description 1
- DGKXRRIUWDMTNX-UHFFFAOYSA-N 2,4,5-tribromo-1-(2-methylpropoxymethyl)imidazole Chemical compound C(C(C)C)OCN1C(=NC(=C1Br)Br)Br DGKXRRIUWDMTNX-UHFFFAOYSA-N 0.000 description 1
- SAVZJULTHDHKCX-UHFFFAOYSA-N 2,4,5-tribromo-1-(hexoxymethyl)imidazole Chemical compound C(CCCCC)OCN1C(=NC(=C1Br)Br)Br SAVZJULTHDHKCX-UHFFFAOYSA-N 0.000 description 1
- YFXDMMDCUGCCGY-UHFFFAOYSA-N 2,4,5-tribromo-1-(methoxymethyl)imidazole Chemical compound COCN1C(Br)=NC(Br)=C1Br YFXDMMDCUGCCGY-UHFFFAOYSA-N 0.000 description 1
- JJYRORJLOMOBKX-UHFFFAOYSA-N 2,4,5-tribromo-1-(propan-2-yloxymethyl)imidazole Chemical compound C(C)(C)OCN1C(=NC(=C1Br)Br)Br JJYRORJLOMOBKX-UHFFFAOYSA-N 0.000 description 1
- MNFDIPKRZDEUMN-UHFFFAOYSA-N 2,4,5-tribromo-1-(propoxymethyl)imidazole Chemical compound C(CC)OCN1C(=NC(=C1Br)Br)Br MNFDIPKRZDEUMN-UHFFFAOYSA-N 0.000 description 1
- VDEPSSNQSCCTJO-UHFFFAOYSA-N 2,4,5-tribromo-1-(propylsulfanylmethyl)imidazole Chemical compound CCCSCN1C(Br)=NC(Br)=C1Br VDEPSSNQSCCTJO-UHFFFAOYSA-N 0.000 description 1
- JCGGPCDDFXIVQB-UHFFFAOYSA-N 2,4,5-tribromo-1h-imidazole Chemical class BrC1=NC(Br)=C(Br)N1 JCGGPCDDFXIVQB-UHFFFAOYSA-N 0.000 description 1
- YNRHCFIOLPTWEW-UHFFFAOYSA-N 2,4,5-trichloro-1-(methoxymethyl)imidazole Chemical compound COCN1C(=NC(=C1Cl)Cl)Cl YNRHCFIOLPTWEW-UHFFFAOYSA-N 0.000 description 1
- XPLCFBYKEIVOPW-UHFFFAOYSA-N 2,4,5-trichloro-1-(propan-2-yloxymethyl)imidazole Chemical compound CC(C)OCN1C(Cl)=NC(Cl)=C1Cl XPLCFBYKEIVOPW-UHFFFAOYSA-N 0.000 description 1
- GXJHZYXSFORYPX-UHFFFAOYSA-N 2,4,5-trichloro-1-(propoxymethyl)imidazole Chemical compound C(CC)OCN1C(=NC(=C1Cl)Cl)Cl GXJHZYXSFORYPX-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FLYDZJXAWKYPFQ-UHFFFAOYSA-N 4,5-dibromo-2,3-dichloro-2-methyl-1H-imidazole Chemical compound ClC1(N(C(=C(N1)Br)Br)Cl)C FLYDZJXAWKYPFQ-UHFFFAOYSA-N 0.000 description 1
- WPGPOYRQEZIAAG-UHFFFAOYSA-N 4,5-dibromo-2-chloro-1-(propoxymethyl)imidazole Chemical compound C(CC)OCN1C(=NC(=C1Br)Br)Cl WPGPOYRQEZIAAG-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241001414900 Anopheles stephensi Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000239223 Arachnida Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241001388466 Bruchus rufimanus Species 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- AQUUDERUHHAECG-UHFFFAOYSA-N C(C)(C)SCN1C(=NC(=C1Br)Br)Br Chemical compound C(C)(C)SCN1C(=NC(=C1Br)Br)Br AQUUDERUHHAECG-UHFFFAOYSA-N 0.000 description 1
- YUIZURZERANZQY-UHFFFAOYSA-N C(C)SCN1C(=NC(=C1Cl)Cl)Cl Chemical compound C(C)SCN1C(=NC(=C1Cl)Cl)Cl YUIZURZERANZQY-UHFFFAOYSA-N 0.000 description 1
- PZLXKLHGTFTZGT-UHFFFAOYSA-N C(C=CC)OCN1C(=NC(=C1Br)Br)Br Chemical compound C(C=CC)OCN1C(=NC(=C1Br)Br)Br PZLXKLHGTFTZGT-UHFFFAOYSA-N 0.000 description 1
- PJNNEKYJYNQQAW-UHFFFAOYSA-N C(CCCCCCC)OCN1C(=NC(=C1Br)Br)Br Chemical compound C(CCCCCCC)OCN1C(=NC(=C1Br)Br)Br PJNNEKYJYNQQAW-UHFFFAOYSA-N 0.000 description 1
- KTAFIZMAAINZAH-UHFFFAOYSA-N CC(C)CSCN1C(Br)=NC(Br)=C1Br Chemical compound CC(C)CSCN1C(Br)=NC(Br)=C1Br KTAFIZMAAINZAH-UHFFFAOYSA-N 0.000 description 1
- ZAZUYYCOEDCDKA-UHFFFAOYSA-N CCSCN1C(Cl)=NC(Br)=C1Br Chemical compound CCSCN1C(Cl)=NC(Br)=C1Br ZAZUYYCOEDCDKA-UHFFFAOYSA-N 0.000 description 1
- LOAHFMZLAONMDI-UHFFFAOYSA-N CSCN1C(Cl)=NC(Br)=C1Br Chemical compound CSCN1C(Cl)=NC(Br)=C1Br LOAHFMZLAONMDI-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241001124134 Chrysomelidae Species 0.000 description 1
- 241000256057 Culex quinquefasciatus Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
- 241001641896 Dermestes lardarius Species 0.000 description 1
- 241001513837 Dermestes maculatus Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000630736 Ephestia Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 241001481698 Mesostigmata Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 241000193804 Planococcus <bacterium> Species 0.000 description 1
- 241000631435 Planococcus minor Species 0.000 description 1
- 241001415279 Pseudococcidae Species 0.000 description 1
- 241001645405 Sarcoptiformes Species 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241001494139 Stomoxys Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241000254107 Tenebrionidae Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001645411 Trombidiformes Species 0.000 description 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical class C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000005432 dialkylcarboxamide group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940070846 pyrethrins Drugs 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/68—Halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH25370A CH485736A (de) | 1967-04-26 | 1967-04-26 | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH25370A CH485736A (de) | 1967-04-26 | 1967-04-26 | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
| CH596067A CH485733A (de) | 1967-04-26 | 1967-04-26 | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH485736A true CH485736A (de) | 1970-02-15 |
Family
ID=4302145
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH25370A CH485736A (de) | 1967-04-26 | 1967-04-26 | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
| CH596067A CH485733A (de) | 1967-04-26 | 1967-04-26 | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
| CH25470A CH485412A (de) | 1967-04-26 | 1967-04-26 | Mittel zur Bekämpfung tierischer und pflanzlicher Schädlinge |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH596067A CH485733A (de) | 1967-04-26 | 1967-04-26 | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
| CH25470A CH485412A (de) | 1967-04-26 | 1967-04-26 | Mittel zur Bekämpfung tierischer und pflanzlicher Schädlinge |
Country Status (14)
| Country | Link |
|---|---|
| US (5) | US3625955A (cs) |
| AT (4) | AT291667B (cs) |
| BE (3) | BE714241A (cs) |
| BR (1) | BR6898630D0 (cs) |
| CA (1) | CA928306A (cs) |
| CH (3) | CH485736A (cs) |
| DE (2) | DE1770270A1 (cs) |
| DK (2) | DK125565B (cs) |
| ES (6) | ES353180A1 (cs) |
| FR (3) | FR1567373A (cs) |
| GB (3) | GB1197102A (cs) |
| IL (3) | IL29886A (cs) |
| NL (3) | NL139313B (cs) |
| SE (3) | SE354176B (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH485736A (de) * | 1967-04-26 | 1970-02-15 | Agripat Sa | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
| CH510394A (de) * | 1969-07-04 | 1971-07-31 | Ciba Geigy Ag | Akarizides Mittel |
| FR2104652A2 (en) * | 1970-04-29 | 1972-04-21 | Agripat Sa | 1-alkoxymethyl-2, 4, 5-trichloroimidazoles - insecticides and acaricides |
| US3934019A (en) * | 1970-12-18 | 1976-01-20 | Bayer Aktiengesellschaft | Pesticidal 4,5-bis-(trifluoromethylimino)-diazoles |
| US4089672A (en) * | 1972-12-20 | 1978-05-16 | The Upjohn Company | 1-(Substituted-hydrocarbyl)-di- and trihalopyrazoles |
| DE2314985A1 (de) * | 1973-03-26 | 1974-10-17 | Hoechst Ag | 1-(imidazol-1-yl)-isochinoline und verfahren zu ihrer herstellung |
| NZ178996A (en) * | 1974-11-15 | 1978-06-02 | Kornis G | Pyrfazole amides and thioamides;herbicidal compositions |
| AU2241677A (en) * | 1976-03-12 | 1978-08-24 | Bayer Ag | 4,5-dichloroimidazole-2-carboxylic acid derivatives |
| DE2646143A1 (de) * | 1976-10-13 | 1978-04-20 | Bayer Ag | 4,5-dichlor-imidazol-1-carbonsaeure- arylester, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
| DE2646144A1 (de) * | 1976-10-13 | 1978-04-20 | Bayer Ag | 4,5-dichlor-imidazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
| DE2646142A1 (de) * | 1976-10-13 | 1978-04-20 | Bayer Ag | 1-acyloxymethyl-4,5-dichlor- imidazol-2-carbonsaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
| US4185991A (en) * | 1976-10-13 | 1980-01-29 | Bayer Aktiengesellschaft | 4,5-Dichloro-imidazole derivatives and their use as herbicides |
| US4187100A (en) * | 1976-10-13 | 1980-02-05 | Bayer Aktiengesellschaft | 4,5-Dichloro-imidazole-1-carboxylic acid aryl esters and their use as herbicides |
| EG17668A (en) * | 1984-11-22 | 1990-08-30 | Sumitomo Chemical Co | Process for preparing of a bromodichlorimidazole insecticide |
| JPS6239577A (ja) * | 1985-08-15 | 1987-02-20 | Sumitomo Chem Co Ltd | トリハロイミダゾ−ル誘導体、その製造法およびそれを有効成分とする殺虫剤 |
| DE3828208A1 (de) * | 1988-08-19 | 1990-02-22 | Basf Ag | Substituierte 2-chlorimidazolderivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide mittel |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567084A1 (de) * | 1963-07-01 | 1970-10-15 | Shell Int Research | Mittel zur Bekaempfung unerwuenschten Pflanzenwuchses |
| US3501286A (en) * | 1964-06-29 | 1970-03-17 | Shell Oil Co | Plant growth control |
| DE1294086B (de) * | 1964-08-07 | 1969-04-30 | Shell Int Research | Herbizide Mittel |
| GB1154722A (en) * | 1965-07-08 | 1969-06-11 | Boots Pure Drug Co Ltd | 2,4,5-Tribromoimidazole Derivatives and Compositions thereof |
| US3409606A (en) * | 1965-12-30 | 1968-11-05 | American Cyanamid Co | Halogenated chloroimidazole compounds |
| US3435050A (en) * | 1966-04-08 | 1969-03-25 | Dow Chemical Co | 2,4,5-trichloroimidazole and method of preparation |
| FR1494338A (fr) * | 1966-07-29 | 1967-09-08 | Chimetron Sarl | Sulfénylimidazoles |
| CH485736A (de) * | 1967-04-26 | 1970-02-15 | Agripat Sa | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
-
1967
- 1967-04-26 CH CH25370A patent/CH485736A/de not_active IP Right Cessation
- 1967-04-26 CH CH596067A patent/CH485733A/de not_active IP Right Cessation
- 1967-04-26 CH CH25470A patent/CH485412A/de not_active IP Right Cessation
-
1968
- 1968-04-24 US US723904A patent/US3625955A/en not_active Expired - Lifetime
- 1968-04-24 US US723903A patent/US3625953A/en not_active Expired - Lifetime
- 1968-04-25 ES ES353180A patent/ES353180A1/es not_active Expired
- 1968-04-25 GB GB19570/68A patent/GB1197102A/en not_active Expired
- 1968-04-25 DK DK189168AA patent/DK125565B/da unknown
- 1968-04-25 ES ES353178A patent/ES353178A1/es not_active Expired
- 1968-04-25 SE SE05584/68A patent/SE354176B/xx unknown
- 1968-04-25 BE BE714241D patent/BE714241A/xx unknown
- 1968-04-25 FR FR1567373D patent/FR1567373A/fr not_active Expired
- 1968-04-25 SE SE05585/68A patent/SE354072B/xx unknown
- 1968-04-25 IL IL29886A patent/IL29886A/xx unknown
- 1968-04-25 FR FR1567374D patent/FR1567374A/fr not_active Expired
- 1968-04-25 BE BE714240D patent/BE714240A/xx unknown
- 1968-04-25 GB GB19569/68A patent/GB1197101A/en not_active Expired
- 1968-04-25 DE DE19681770270 patent/DE1770270A1/de active Pending
- 1968-04-25 GB GB19571/68A patent/GB1197103A/en not_active Expired
- 1968-04-25 ES ES353179A patent/ES353179A1/es not_active Expired
- 1968-04-25 NL NL686805901A patent/NL139313B/xx unknown
- 1968-04-25 DK DK189368AA patent/DK125284B/da unknown
- 1968-04-25 ES ES353177A patent/ES353177A1/es not_active Expired
- 1968-04-25 DE DE1770269A patent/DE1770269C3/de not_active Expired
- 1968-04-25 ES ES353181A patent/ES353181A1/es not_active Expired
- 1968-04-25 AT AT492969A patent/AT291667B/de not_active IP Right Cessation
- 1968-04-25 IL IL29888A patent/IL29888A/xx unknown
- 1968-04-25 FR FR1567372D patent/FR1567372A/fr not_active Expired
- 1968-04-25 NL NL6805900A patent/NL6805900A/xx unknown
- 1968-04-25 ES ES353182A patent/ES353182A1/es not_active Expired
- 1968-04-25 SE SE05586/68A patent/SE352804B/xx unknown
- 1968-04-25 AT AT403968A patent/AT280279B/de not_active IP Right Cessation
- 1968-04-25 AT AT404068A patent/AT280280B/de active
- 1968-04-25 NL NL6805899A patent/NL6805899A/xx unknown
- 1968-04-25 AT AT404168A patent/AT280692B/de not_active IP Right Cessation
- 1968-04-25 BE BE714239D patent/BE714239A/xx unknown
- 1968-04-25 IL IL29887A patent/IL29887A/en unknown
- 1968-04-25 CA CA018359A patent/CA928306A/en not_active Expired
- 1968-04-25 BR BR198630/68A patent/BR6898630D0/pt unknown
-
1970
- 1970-06-08 US US44558A patent/US3674874A/en not_active Expired - Lifetime
-
1971
- 1971-04-05 US US00131447A patent/US3773960A/en not_active Expired - Lifetime
- 1971-06-28 US US00157698A patent/US3759945A/en not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |